Why Jordan Never Demos on Day One (adn teh Catastrophe of Max’s Misstep)

Navigating the treacherous waters of technical sales is akin to diffusing a bomb while blindfolded. You learn quickly or you don’t survive. Jordan, my sagely mentor with a penchant for dramatic truths, taught me one golden rule over our many post-mortem pub sessions: Never, ever demo on day one.

It’s not superstition; it’s about avoiding spontaneous combustion.

I learned this lesson in the most painful way imaginable at Tyrell Tech. Just recalling the event makes me grimace, a movement not unnoticed by my long-suffering coffee mug.

Riley, with his perpetual boyish enthusiasm, was spearheading the Tyrell account. “They’re practically ours,” he chirped, practically tap-dancing with glee. “Just needs a bit of technical fluff. Easy peasy.”

In my notebook, I scribbled: Easy peasy in Riley-speak means prepare for Armageddon.

“What exactly are they expecting?” I ventured, already bracing for impact.

“Just a peek at the platform. Their CTO’s a bit hands-on,” Riley grinned, an optimism so bright it could cause sunburn. “I’ve penciled you in for tomorrow. Nothing bespoke, just run-of-the-mill stuff.”

That should have been my cue to run for the hills. In the murky realms of tech demos, ‘run-of-the-mill’ is as common as a unicorn.

“And who are we entertaining?” I probed, visions of late nights dancing in my head.

“Just the key players,” replied Riley, which inevitably meant everyone including the office cat.

That night, I prepared what I believed was an invincible demo. Environments double-checked, sample data triple-loaded, and backup slides up the wazoo. I rehearsed till the words lost all meaning. I was a warrior ready for battle.

The next morning, I logged into the Zoom call prematurely, exuding a caffeinated blend of professionalism and sheer terror. The Tyrell brigade arrived in dribs and drabs - first the CTO, Eldon, followed by a conga line of various titles and faces that I would inevitably forget.

Once the pleasantries were dispensed with, I launched into my spiel. “I gather you’re keen to see our real-time data-processing prowess across complex systems?”

Eldon nodded. “Particularly keen on the compliance module. It’s critical for our operations.”

My stomach performed an Olympic-level flip. Riley had conveniently omitted any mention of ‘compliance.’

“Absolutely,” I fibbed with a smile plastered on. “Let’s dive into that.”

Technically, the demo was a symphony of perfection. The software performed its dance flawlessly, dazzling with data and dazzling the onlookers - especially with my horrendous joke about “SELECT * FROM problems,” which surprisingly tickled the CTO.

Then disaster struck in the form of a seemingly innocent question.

“This is splendid,” Eldon leaned in, all interest piqued. “Could you demonstrate the data residency controls? Sandra from Legal will need to give the nod.”

I kept my smile stitched on. “Of course. The platform boasts extensive data residency controls.” I navigated to the relevant screen. “Here, policies can be tailored at multiple levels.”

“Marvelous,” Eldon beamed. “Sandra will be thrilled. She’s particular about these things.”

“Is Sandra joining us today?” I ventured, hoping to directly address any of her potential anxieties.

A pause swelled, filling the room like an unwelcome guest. Then Eldon chuckled. “Oh, Sandra’s on a sabbatical. Scaling mountains in Nepal. Completely off-grid. She’ll be back next month.”

My smile fossilized. “And… she’s the sole signatory?”

“Indeed,” Eldon’s cheerfulness did nuthin to ease the sinking feeling. “Nothing moves without Sandra’s stamp.”

There it was. The deal’s death knell. Sandra, Legal’s gatekeeper, was communing with the heavens, beyond the reach of mundane things like email.

“Does she have a deputy?” I asked, a thread of hope in my voice.

Eldon laughed, a sound that echoed the death of our commission. “Sandra doesn’t do deputies.”

The rest of the call was a blur, a like molasses-motion trainwreck. Promises were made about sending over documents for Sandra’s eventual perusal - documents that would sit idly, waiting for her royal stamp of approval.

As soon as the call ended, Riley pinged me: Nailed it! They loved us!

I stared at the screen. Had Riley been on the same call, or had he transcended into a parallel universe where Sandra was not an absentee monarch?

Riley, I typed, fighting the urge to scream, we just demoed to a ghost. Sandra’s approval method? A stamp. She’s back next quarter.

His reply: So, we’re still in the game?

Later, Jordan found me nursing my coffee, my face a study in despair.

“How did Tyrell go?” they inquired.

“Ever tried selling a dream to a phantom?” I muttered.

Jordan nodded, the ghost of a smile playing on their lips. “Ah, the elusive stakeholder. Classic. Someone vital, unreachable?”

“Sandra’s off embracing her inner yeti in Nepal. No contact, just a desk waiting for her stamp.”

Jordan’s smirk was all-knowing. “That’s why day one is for reconnaissance, not show-and-tell. You find all the Sandras before they find you.”

I added a new note to my battered notebook: Rule #1 (reinforced): Never demo on day one. Sandras lurk everywhere, sometimes even in the Himalayas.

The next time Riley approached, buzzing about another “simple validation,” I simply smiled. “Who’s your Sandra this time?”

His confusion was palpable, but I had learned. There’s always a Sandra. And occasionally, she’s incommunicado, possibly consulting with mountain spirits.